过渡金属催化不对称C—H硼化反应研究进展

doi:10.6023/cjoc202308001

摘要/Abstract

过渡金属催化不对称C—H硼化反应是构建手性有机硼化合物最为有效的策略之一, 具有原子和步骤经济性, 在合成化学、药物化学和材料学等领域受到广泛关注. 新型手性配体的设计与合成是过渡金属催化不对称C—H硼化反应成功的关键, 根据手性配体的设计和发展过程, 对近年来实现的过渡金属催化不对称C(sp²)—H和C(sp³)—H硼化反应的研究进展进行综述.

关键词: 不对称C—H硼化, 手性配体, 过渡金属配合物

Transition-metal-catalyzed asymmetric C—H borylation is one of the most powerful strategies for the construction of chiral organoborate compounds, which has attracted extensive attention in the fields of synthetic chemistry, medicinal chemistry and materials science due to its atom- and step-economy. The design and synthesis of novel chiral ligands are essential for the success of asymmetric C—H borylation. Based on the design and development of chiral ligands, the recent progress of transition-metal-catalyzed asymmetric C(sp²)—H and C(sp³)—H borylation reactions is summarized.

Key words: asymmetric C—H borylation, chiral ligand, transition metal complex

引用此文

王文芳. 过渡金属催化不对称C—H硼化反应研究进展[J]. 有机化学, 2023, 43(9): 3146-3166.

Wenfang Wang. Recent Progress in Transition-Metal-Catalyzed Asymmetric C—H Borylation[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3146-3166.

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图/表 32

图式1. 不对称C(sp2)—H和C(sp3)—H硼化反应

Scheme 1. Asymmetric C(sp2)—H borylation and C(sp3)—H borylation

图式2. 铱催化芳烃C(sp2)—H硼化的一般催化循环

Scheme 2. A general catalytic cycle for the borylation of aryl C(sp2)—H catalyzed by an iridium catalyst

图式3. 硅基导向的铱催化对映选择性芳基C—H硼化反应

Scheme 3. Silyl-directed iridium-catalyzed enantioselective borylation of aryl C—H bonds

图式4. 铱/Py-DHIQ体系催化对映选择性芳基C—H硼化反应

Scheme 4. Enantioselective borylation of aryl C—H bonds catalyzed by iridium/Py-DHIQ system

图式5. 非手性双齿N,B配体/铱体系催化对映选择性芳基 C—H硼化反应及新型手性双齿N,B配体骨架

Scheme 5. Enantioselective borylation of aryl C—H bonds catalyzed by achiral bidentate N,B ligand/iridium system and novel chiral bidentate N,B ligand skeleton

图式6. 使用手性双齿N,B配体的铱催化不对称C(sp2)—H硼化反应

Scheme 6. Chiral N,B-bidentate ligand enabled iridium-cata- lyzed asymmetric C(sp2)—H borylation

图式7. 前手性二芳基甲胺对映选择性C(sp2)—H硼化反应的部分底物拓展

Scheme 7. Representative substrate scope of enantioselective C(sp2)—H borylation of prochiral diarylmethylamines

Entry	R¹, R², R³	Conv./%	ee(6')/%	ee(5')/%	s^a
1	CF₃, CF₃, H	30	94	41	68
2	CF₃, CF₃, 3-Me	30	90	40	25
3	OMe, OMe, H	33	85	42	19
4	OMe, CF₃, 3-Cl	50	88	88	45
5	CF₃, CF₃, 4-Cl	54	72	62	9

表1. 消旋二芳基甲胺C(sp2)—H硼化反应动力学拆分的部分底物

Table 1. Representative substrate scope of kinetic resolution of C(sp2)—H borylation of racemic diarylmethylamines

图式8. 前手性二芳基磷酸盐对映选择性C(sp2)—H硼化反应的部分底物拓展

Scheme 8. Representative substrate scope of enantioselective C(sp2)—H borylation of prochiral diarylphosphinates

图式9. 铱/L6体系催化对映选择性C(sp2)—H硼化反应的部分底物拓展

Scheme 9. Representative substrate scope of enantioselective C(sp2)—H borylation catalyzed by iridium/L6 system

Entry	B₂pin₂/equiv.	10a∶I∶II∶III^a	Yield^a/%	ee^b/%
1	1.00	87.6∶0.0∶9.9∶2.5	91 (83)^c	92
2	0.50	98.8∶0.0∶1.2∶0.0	65	87
3	0.75	96.2∶0.0∶3.1∶0.7	88	88
4	1.30	57.7∶0.0∶38.8∶3.5	53 (52)^c	96

表2. B2pin2用量对二苯基甲基醚对映选择性C(sp2)—H硼化反应的影响

Table 2. Effect of B2pin2 dosage on enantioselective C(sp2)—H borylation of benzhydryl ethers

图式10. 铱/L7体系催化对映选择性C(sp2)—H硼化反应的部分底物拓展

Scheme 10. Representative substrate scope of iridium/L7 system catalyzed enantioselective C(sp2)—H borylation

图式11. 阴离子配体、手性阳离子、离子对配合物及对映选择性远端C(sp2)—H硼化反应

Scheme 11. Anionic ligands, chiral cation, ion-paired complexes and enantioselective remote C(sp2)—H borylation

图式12. 二芳基酰胺类和二芳基膦酰胺类化合物对映选择性C(sp2)—H硼化反应的部分底物拓展

Scheme 12. Representative substrate scope of enantioselective C(sp2)—H borylation of benzhydrylamides and diaryl phosphinamides

图1. 手性吡啶类配体CP1和CP5及手性吡啶衍生双齿N,B-配体骨架

Figure 1. Chiral pyridine-type ligands CP1 and CP5 and chiral pyridine-derived bidentate N,B-ligands skeleton

图式13. 三芳基甲烷化合物部分底物拓展

Scheme 13. Representative substrate scope of triarylmethanes

图式14. 二茂铁部分底物拓展

Scheme 14. Representative substrate scope of ferrocene

图式15. Pd(II)催化的对映选择性环状底物亚甲基C(sp3)—H硼化反应

Scheme 15. Pd(II)-catalyzed enantioselective borylation of methylene C(sp3)—H in cyclic substrates

图式16. 铱催化的环丁烷对映选择性C(sp3)—H硼化反应

Scheme 16. Iridium-catalyzed enantioselective C(sp3)—H borylation of cyclobutanes

图式17. 铱催化的环丙烷甲酰胺对映选择性C(sp3)—H硼化反应

Scheme 17. Iridium-catalyzed enantioselective C(sp3)—H borylation of cyclopropanecarboxamides

图式18. C—B键转化合成左旋米那普仑

Scheme 18. Synthesis of Levomilnacipran through C—B bond conversion

图式19. [Ir(OMe)(cod)]2/L13体系催化氨基环丙烷对映选择性C(sp3)—H硼化反应

Scheme 19. [Ir(OMe)(cod)]2/L13 system catalyzed enantioselective C(sp3)—H borylation of aminocyclopropanes

图式20. [Ir(cod)Cl]2/L14体系催化氨基环丙烷对映选择性C(sp3)—H硼化反应

Scheme 20. [Ir(cod)Cl]2/L14 system catalyzed enantioselective C(sp3)—H borylation of aminocyclopropanes

图式21. [Ir(cod)Cl]2/L14体系催化环丙醇衍生物对映选择性C(sp3)—H硼化反应

Scheme 21. [Ir(cod)Cl]2/L14 system catalyzed enantioselective C(sp3)—H borylation of cyclopropanol derivatives

图式22. Ir—O桥联催化设想

Scheme 22. Ir—O bridging catalytic hypothesis

图式23. 铱催化醚基环丙烷对映选择性C(sp3)—H硼化反应

Scheme 23. Iridium-catalyzed enantioselective C(sp3)—H borylation of ether cyclopropane

图式24. 铱催化四氢异喹啉类对映选择性C(sp3)—H硼化反应

Scheme 24. Iridium-catalyzed enantioselective C(sp3)—H borylation of THIQ

图式25. 铱催化氮杂环类对映选择性C(sp3)—H硼化反应

Scheme 25. Iridium-catalyzed enantioselective C(sp3)—H borylation of azacycles

图式26. 铱催化吡唑类对映选择性C(sp3)—H硼化反应

Scheme 26. Iridium-catalyzed enantioselective C(sp3)—H borylation of pyrazoles

图式27. 铱催化无环酰胺类对映选择性C(sp3)—H硼化反应

Scheme 27. Iridium-catalyzed enantioselective C(sp3)—H borylation of acyclic amides

图式28. 通过烯烃异构化实现钴催化内烯烃不对称远端C(sp3)—H硼化反应

Scheme 28. Cobalt-catalyzed asymmetric remote C(sp3)—H borylation of internal alkenes via alkene isomerization

图式29. 钴催化卤代烃不对称远端C(sp3)—H硼化反应

Scheme 29. Cobalt-catalyzed asymmetric remote C(sp3)—H borylation of alkyl halides

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